Dry cleaning solvent containing a bleach

ABSTRACT

THIS APPLICATION RELATES TO DRYCLEANING SOLVENTS CONTAINING N-BROMO OR CHLORO-N-ALKYL CARBOXAMIDES, OR THE NCHLORO AND N-BROMO DERIVATIVES OF 2-OXAZOLIDINONE, 2MORPHOLINONE AND 2-OXAZINIDINONE AS BLEACHING AGENTS.

\JL-LLLU uscu'vu J. wbvnt O ABSTRACT OF THE DISCLOSURE This applicationrelates to drycleaning solvents containing N-bromo or chloro-N-alkylcarhoxamides, or the N- chloro and N-bromo derivatives of2-oxazolidinone, 2- morpholinone and 2-oxazinidinone as bleachingagents.

BACKGROUND OF THE INVENTION Compounds having the formula such as RN%-H Xwherein each R is the same or different alkyl radical havchlorine arevery active and easily reduced. They are too unstable, however, to beused as bleaching agents in commercial drycleaning solvents.

SUMMARY OF THE INVENTION The products of this invention are drycleaningsolvents containing (1) carboxamide compounds having the formula whereineach R is the same or different alkyl radical having from 1 to 8 carbonatoms or (2) carboxamide corn pounds having the formula wherein A is -O,(CH;),, wherein n=l-3, -CH O, or OCH X is chlorine or bromine; R and Rare each hydrogen, alkyl of 1-4 carbon atoms or phenyl; and R and R, areeach hydrogen or alkyl of 1-4 carbon atoms.

Useful carboxamide compounds include, for example, the N-halo-N-alkylcarboxamides such as N-chloro-N- methyl acetamide, N-chloro-N-butylbutyramide, N-chloro-N-methyl caprylamide and N-bromo-N-propylcaproamide; the N-halo-2-oxazolidinones such as N-chloro-S- methyl 2oxazolidinone, N-bromo 5 methyl 2 oxazolidinone,N-chloro5-ethyl-2-oxazolidinone, and N-chloro-2-oxazolidinone; theN-halo-3-morpholinones such as N-chloro-3-morpholinone; theN-halocaprolactams such as N-chlorocaprolactam; the N-halo2-pyrrolidinones such as N-chloro-2-pyrrolidinone, and theN-halo-2-imidazolidinones such as N-chloro 4-imidazolidinone. Suchcompounds are readily prepared by reacting the nonhalogenatedcarboxamide with a halogenated isocyanuric acid as illustrated incopending application Ser. No. 679,227 filed Oct. 30, 1967, by W. E.Walles and entitled Transhalogenation of Imides. These compounds arerelatively stable to antooxidation and have been found to be eminentlysuitable for use as bleaching agents in drycleaning solvents. The activecompounds as well as the residue remaining after they have been employedas the bleaching ice agent are very soluble in the common drycleaningsolvents.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The preferred carboxamidecompounds to employ in the compositions of this invention are thosewherein each R is methyl or ethyl, the most preferred compound beingN-chloro-N-methyl acetamide. The N-chloro-N-alkyl carboxamides may beprepared by reacting trichlorocyanuric acid with the desired N-alkylcarboxamide at temperatures of about to 60 C., and they may be purifiedby distillation or other known means.

The invention is further illustrated by the following example.

Example N-chloro-N-methyl acetamide (B.P. 43-44 C. at 25 mm. pressure)was prepared by reacting 73 grams (1.0 mol) of N-methyl acetamide with77 grams (0.33 mol) of trichlorocyanuric acid at 40 to 52 C. The productwas purified by distillation at atmospheric pressure.

A solution of 4% by weight of N-chloro-N-methyl acetamide in methylchloroform containing in addition 2% by weight of water was heated to 60C. and a 2" square piece of unbleached cotton cloth was left in cc. ofthe heated solution for one hour. The cotton was bleached white.

A similar test was carried out using freshly prepared paper from asulfite pulp which had been prebleached by the chlorine extractionsystem. Before treatment the paper was grayish tan and after bleachingfor one hour it was slightly off-white.

Similar results are obtained by employing N-chloro-N- ethyl acetamide,N-chloro-N-propyl acetamides, the N- ChlOTONrbUlYl acetamides,N-chloro-5-methyl-2-oxazolidinone, N-chloro S-ethyl 2-oxazolidinone,N-chloro-Z- oxazolidinone, N-chloro-S-morpholine, N-chlorocaprolactam.N-chloro 2-pyrrolidinone, chloro-4-methyl-2-imidazolidinone andN-bromo-5-methyl-2 oxazolidinone, and the like.

The bleaching agents of this invention are very soluble and effective inall of the common drycleaning and degreasing solvents such as, forexample, methylene chloride, perchloroethylene, trichloroethylene,carbon tetrachloride, and the like.

We claim:

1. A drycleaning composition consisting essentially of a solventselected from the group consisting of methylene chloride,perchloroethylene, trichloroethylene, carbon tetrachloride ormethylchloroform and a bleaching agent in a bleaching amount of acompound having the formula wherein each R is the same or differentalkyl radical having from 1 to 8 carbon atoms, X is chlorine or bromine,A is -O-, (CH wherein n is 1-3, CH O or OCH R and R are each hydrogen oralkyl of 14 carbon atoms and R and R are each hydrogen or alkyl or l-4carbon atoms.

2. Process for bleaching cotton which comprises treating said cottonwith a solvent selected from the group consisting of methylene chloride,perchloroethylene, trichloroethylene, carbon tetrachloride andmethylchlord form, said solvent consisting essentially of a bleachingagent in a bleaching amount of a compound having the carbon atoms and Rand R are each hydrogen or alkyl formula of 1-4 carbon atoms.

3. Process of claim 2 wherein the bleaching agent em ployed isN-chloro-N-methyl acetamide. RN-CR R,c-- A 5 4. Process of claim 3wherein the solvent is methyl- (3:0 chloroform.

References Cited 4 Chem. Abstracts, v01. 64, 11123a-11123h, April 1966.

wherein each R is the same or different alkyl radical hav- 10 MAYERWEINBLATT Pnmary Examiner ing from 1 to 8 carbon atoms, X is chlorine orbromine, U S C1 X R A is O, -(CH wherein n is 1-3, CH O or -OCH R and Rare each hydrogen or alkyl or 1-4 l 142 mg UNITED STATES PATENT OFFICECERTIFICATE OF CORRECTION Patent No. 3,57 ,7 Date l 7 April 97 Inv r-(Wilhelm E. Walles and Elton D. Prueter It is certified that errorappears in the above-identifier! patent and that said Letters Patent arehereby corrected as shown below:

In column 1, line 2 4, delete "each R is the same or different alkylradical hav-" and insert R is an alkyl grouo and X is either bromine orIn line 62, change l-imidazolidinone" to l-methyl-Z-imidazolidinoneSigned and sealed this 31 at day of August 1971 (SEAL) Attest:

EDWARD M.FLETCHER, JR. Attesting Officer WILLIAM E. SCHUYLER, JR.Commissioner of Patents

